The start of this story happens one day when my friend Matt was over to our house shooting hoops in the driveway. My mother had just pulled her car into the garage interrupting our game of horse. Matt had never tried to hide the fact that he flirts with my mom whenever she is around and today is no different.
"Here let me get the door for you Donna, do you have any bags I can help you with?" He asked her opening her door all the way for her.
"No Matt, thanks anyway, all I have today is this little one from the pharmacy." She said to him.
Mom had always thought Matt to be a sweet boy and never really seemed to notice his flirting, it either went over her head or she did not think anything of it. I seem to be the only one who notices, my father might notice, cause sometimes he seems to just snort and chuckle to himself when he hears Matt come on strong.
"C'mon Matt let's get back to our game, I only need to get one more letter for the win." I said.
"Well see you later Donna, I have to stage one of my patented amazing come backs to beat Jimmy over there." He said letting my mother by him.
"Have fun." She said and went into the house.
After she was in the house and out of ear shot, I took a shot that bounced off the rim; Matt grabbed and dribbled over to me. I knew what he wanted to talk about, heck deep down I liked talking about her too.
"Man, dude, your mom sure is hot for forty four years old." He said standing there dribbling.
"She's not bad if you compare her to other mothers from our school." I said to him.
"How big did you say her tits were?" He asked wanting me to refresh his memory.
"38C" I simply stated.
"Nice, her ass looks awesome in everything she wears and I love those short skirts she wears to work." He said finally taking a shot.
"Man do you jerk off a hundred times a week thinking of my mom?" I asked him retrieving the ball.
"Oh yeah like you don't" He said. "Did you see what she had in the prescription bag?"
"No, I was not looking; I was trying to finish this game before dinner." I said to him.
"That new heavy duty sleeping pill, the one that puts you out for eight hours a night, I heard they are quite potent." Matt said.
"Well she said with the company she works for cutting back she had to let some of her office staff goes. She is really tired and stressed when she gets home, combined with my dad's snoring she has been complaining she is not getting enough sleep at night." I explained to him.
"I tell you what, I'm going to take off, tomorrow let know how well they work." He said and he ran off for home.
We were both eighteen years old and as far as knew we were both virgins, neither of us getting past second base. I think we spent too much time fixating on milfs and older women rather than girls our own age. So I was going to make sure when mom got up the next morning I would find out if she got a good night sleep, I was unsure why he wanted to know, unless he was thinking of getting some.
Dinner was uneventful; mom was tired and did not feel much like talking, so offered to do the dishes for her so she could rest. Dad got home late and then announced that he was going to Chicago for a weekend meeting to try and close a huge contract with another company.
"Well Bill I know how you are on the road, so stick to your diet." Mom said to him.
"Donna, I'll try my best you know it's hard to eat salad in a steak house." He laughed.
Mom was always nagging dad on his weight, unlike her he put on weight during the marriage. His doctor said that is why he snores so much and loudly, plus he was in danger of high blood pressure and other health risks. Mom told him for her birthday this year she wanted him to lose twenty pounds, he still had four months to go but was no where close.
I took all of the dirty dishes out to kitchen, my mother packed my dad's bag and he got all of his files and his laptop together. She then changed for bed and took one of her pills, the next morning dad was up first, and I heard him grumbling at four in the morning going down the stairs with his bags. His taxi got there a half an hour after that to pick him up, a few hours later my mother and I were up getting ready for work and school.
"Oh mom by the way how did you sleep last night?" I asked her before she went out the door for work.
"The best night's sleep I have had in ages, I did not even hear your dad's snoring. Love you and see you later." She said hurrying out.
During lunch at school Matt and I sat together watching a pick up game in the gym; he had been pestering me all day for information on how my mother slept. I still found it weird why he wanted to know, but I gave him the information he wanted.
"She said she got the best night's sleep she had gotten in years." I told him.
"Call her and ask if I can spend the weekend, starting tonight?" He anxiously asked.
"Sure what the heck she is on her lunch break anyhow." I said pulling out my cell and text messaged my mother.
"So what did she say?" He asked when he heard the phone chime back.
"She said sure you can, just as long as we are quiet when she goes to bed." I explained.
"Cool, so this being Thursday, I will need to stop at my house and get a few things for the next few days." Matt said.
"Okay, when you are done I will see you at my house." I said as the bell rang signaling us to get to class.
After school I went home as usual, worked on homework to get it done before Matt arrived. He got there shortly before my mom arrived home, she called me on the phone to let me know she got pizza for dinner and to meet her in the driveway to carry it in.
"I'll go get it." Matt offered running out to help my mother.
I watched as she handed him the pizza and he followed her into the house, his eyes never leaving her swaying ass. We sat at the table to eat; mom only had one slice and made a small salad, staying on her diet. The two of us chewed down heartily on the pizza, I listened to Matt's constant flirting and compliments to my mother.
"Jimmy you should take lessons from Matt on how to compliment a lady." My mom said embarrassing me.
"Sure Mom, just remember Matt has had the same amount of girlfriends as I have this past school year." I said making him turn red.
"Don't worry boys; I'm sure the right young lady will come along. I have some work to catch up on and then I have to call your dad. I will probably be turning in around nine so remember that is time to quiet down." She said to us.
We stayed out of her way the rest of the night and played video games in my room, sure enough at nine my mother looked in on us. She was wearing a pair of silk pajamas and it obvious she did not have a bra on.
"Good night boys, I'm going to turn in." She said.
"Good night Mom."
"Good night Donna." Matt said. "Sweet dreams."
An hour had passed and finally Matt got up and he crept down the hall way to the bathroom. He opened the medicine cabinet and pulled out the prescription bottle and counted the pills. Then with a smile on his face he came back into my room and sat down.
"I say let's give it another hour and let's see how asleep your mom really is." He said.
"Are you fucking nuts?" I exclaimed.
"Dude this will be the best time to find out." He said. "She definitely took a pill tonight and if they are as good as advertised this should be interesting."
"Alright, if we do anything you better let me go in first and see if she wakes, I can come up with an excuse for being in there." I explained to him.
"You got a deal" He said as we went back to playing for another hour.
At eleven o' clock we crept down the hall and slowly opened her bedroom door and crept into her room. We could hear her heavy breathing from across the bedroom as she slept soundly. I slowly went up to her bed and gently shook her shoulder, then again, and then a third times a little harder and said mom in a low voice.
"See I told you she was out." Matt said.
"So what are you going to do?" I asked him.
"We have to see those titties of hers." He said reaching down with trembling hands.
Slowly he undid the top button, then the next one to reveal more and more of her ample cleavage. The way the silk moved against her skin made her nipples start to harden against the fabric. He the undid another, then another, the top only had five buttons and left the last one together and slowly slid if off to her shoulders to expose her beautiful breasts.
"Holy shit, those have to be the best tits I have ever seen." Matt exclaimed softly.
"I can't believe I'm standing here looking at my mother's tits." I whispered.
Matt then reached down and touched the one furthest away from him, a light gentle caress over the full length of it. Then he lightly brushed the nipple, which was now hard from the cooler air and the stimulation. He surprised me when he gave it a gentle squeeze, then he gave the other one a gentle squeeze, then he rubbed the nipple. This made my mother moan aloud in her sleep, she must be enjoying the stimulation as she showed no sign of waking.
"You have to feel them; you won't believe how firm they are." He said moving his hand away to let me feel.
Hesitantly I reached down and ran my hand over her left breast, enjoying how soft her skin felt. I took her nipple and pinched it while marveling at how hard it was, then I gave the breast a gentle squeeze, he was right very firm. I continued to alternate playing with her tits, while Matt ran his hand down to her pajamas bottom.
His hand slowly crept inside, he smiled as he worked his way down over her mound, and her legs were slightly spread so he had access to her pussy. My mother let out another moan and you could see a look of pleasure on her face as her lips were now open in a little o.
"She is sopping wet and she just has a landing strip of hair." He said rubbing her pussy.
"Wow, I want to suck on her tits, while you rub her pussy." I said leaning down toward them.
"Fuck, you are really getting hot over your mom." Matt said as he found her clit and was vigorously rubbing it.
I ignored the comment and went to vigorously suck and squeeze her tits; I licked and nibbled her nipples. While I sucked one I squeezed the other, harder than I did when I first touched them. My mother was now moaning aloud in her sleep and her pussy was now bucking against Matt's hand.
"Mmmm cumming, cumming." She moaned aloud followed my one long moan.
"Shit we got her off, we better button her back up, besides I have to take care of this wicked boner I have." I told Matt as his hand reluctantly pulled out of her bottoms.
We quickly buttoned her back up and left her to resume her peaceful sleep and we hurried back to my room. We wasted no time whipping our dicks out; we both came hard and fast, less than thirty seconds. Then we cleaned up and went to bed, Matt told me before we went to sleep that tomorrow would be even better.
The next morning Matt told me he was going to be late coming home with me today, when he finally did arrive he showed me what he had. Inside a brown paper bag was a box of condoms, was he thinking we could actually climb on the bed and fuck my mother.
"Matt do you honestly think we could get away with having sex with my mother?" I asked him.
"You saw last night how out she was, I think we can get away with it, let me go first your mom is so hot I'm willing to take a chance." He said.
"Alright I will let you try, but don't you think she will be able to tell she was fucked last night when she wakes up in the morning?" I asked him.
"Well she might think she got fucked, that is why I got the condoms, and we won't leave any evidence behind." He replied.
"Man you are crazy! I exclaimed.
"Crazy for your mom's sexy body, I can't wait for bedtime." He laughed.
My mother got home a couple hours later, she was tired from work, and she had a long meeting before she had to leave. She made herself a salad and asked if Matt and I could fend for ourselves. We left her to go get some burgers down at the burger stand in town and then we came back a couple hours later.
When we got home mom had wet hair and she was lying on the couch in just her large wooly pink robe. She was relaxed watching a chick flick on cable when I came in and sat on dad's easy chair and Matt sat at the end of the couch making her curl her feet up to the second cushion so he could sit.
"You boys should have dates on a Friday night like this, not hanging out with a tired old lady." She said when the movie went to commercial.
"I got shot down on Thursday, I don't know about Matt." I said.
"Did not even bother, when Matt said I could spend the weekend with him and his attractive mother, I jumped at the chance." Matt said obviously flirting with her.
"Thank you Matthew that is very sweet of you to say." She said. "Well I think after this movie is over I'm going to hit the sack. I have plenty of work to do around here tomorrow and oh I made up a to do list, you guys should be able to get done rather quickly if you work together."
"Thanks Mom." I replied.
An hour later she got up to go to bed, she kissed Matt on the forehead and then she gave me one on the cheek. She left the two of alone downstairs to watch television; we waited a couple of hours and Matt left to go to the bathroom upstairs. No doubt he was going to check and see if she took a sleeping pill.
When he did not come back down after a few minutes, I got up to see what the hell he was up too. I stopped into the bathroom and took her pill bottle out of the medicine cabinet to see if you she took one. It was one less than the night before so she did take one pill and went to bed. Now it was going on one in the morning and I could see my parent's bedroom door half open.
I went down the hall to see Matt standing over my sleeping mother, he was naked, a condom on his hard cock. She was wearing a short silk night shirt tonight, he was playing with her tits, and I could see her hard nipples through the shirt. He slowly pulled the blanket down off of her to reveal her legs which he now slightly spread; mom did not have any panties on.
Matt kept one hand on a tit, massaging it and used his other hand to manipulate her pussy. He was ready to climb on top of her and moved her legs further apart, I could now see he was right and saw that she only maintained a landing strip for pubic hair. He went down to the foot of the bed and climbed up between her legs, slowly edging him up to her waist.
He positioned his cock to the entrance of her pussy; he used one hand to guide it in and one hand to try to keep his weight off of her. Inch by inch he plunged his six inch cock into my mother; I could hear him groan audibly at the pleasure. Mom also let out a long moan that you would hear from a woman having sex.
Matt was now getting excited, he thrust in and out of my mother slowly at first trying not to wake her or cum to fast. But the more he did this the more excited he got, he soon started thrusting faster and faster.
"Oh Donna, Donna, your pussy is so wet and tight." He grunted.
"Mmm, Mmm, Mmmm, Mmmm." My mother moaned softly as she was sleeping and getting fucked by my best friend.
Soon Matt was grunting hard and he moaned aloud, he was now emptying his load into his condom. He slowly finished cumming and then he climbed off of my mother, sweat glistened on his body as he walked towards me.
"Whew, your mom is awesome." He said. "I know I made her cum once."
"I guess I better take a shot at her." I said getting undressed.
"You got your condom right?" He asked.
"Yeah, it's in my pocket." I replied.
I finished getting undressed and put the condom on my already hard cock; my cock is not as long as Matt's but it is thicker. I climbed onto the bed and crawled up her so my cock was now lined up to her pussy. Then I gave it a push and was in all the way in one try, she was very wet still and she groaned when she felt my cock.
Matt was right she was very tight, even after the fucking he had just given her pussy; I felt it contract around my cock and pull it in. I too started out slowly pulling my cock out all the way and then pushing it back in.
"Oh baby, don't tease me with, fuck me hard." She moaned softly in her sleep. "Give it to me Bill."
She must have been dreaming of my dad, thinking he was there in bed with her; I pushed myself back into her and moved my body up on top of her. I pushed her shirt up enough to where I could suck on her nipples as I fucked her. I pounded my cock into her as hard as I could, my mother was grunting with each of my thrusts.
"Oh yes Bill, oh yes, I'm cumming again, oh yes make me cum." She said.
That was all I needed to hear, simultaneously my mother and I came together. I took my time trying to catch my breath as I slowly climbed off my mother.
"That was great Bill, but honey I really need my sleep." She said pulling the blanket back around her.
Matt came back in with a can of air freshener and he sprayed it around is small quick spurts. I understood what he was doing, he did not want my mother waking up and finding the bedroom smelling like sex.
"Wow, you were right and she thought she was fucking my dad when I was going at it with her." I said.
"You know what is cool; we still have Saturday to fuck her again." Matt said.
"Do you think she will take a sleeping pill on the weekend, she might not need one?" I said to him.
"Be an optimist, now I don't know about you but I'm going to get some sleep, goodnight motherfucker." He said.
"Goodnight motherfucker." I replied laughing.
The next morning we awoke to the smell of bacon and home fried potatoes being made in the kitchen. When went downstairs we found my mother as the stove making breakfast for us. She was dressed in what we called her house work clothes, a pair of loose fitting sweat pants and an old tee shirt of dads.
"Good morning guys, I have pancakes, bacon, sausage and home fries for you guys so you can get this nice long list of chores done today." She said as we sat down.
"Wow this looks great Donna." Matt said.
"Yeah mom, those pills most be doing wonders for you, you have not had this much energy in a long time." I said.
"I know last night was the most in credible night's sleep I had gotten in years." She said putting the last of the food down and sitting in front of her grapefruit.
"Well I guess we better eat up, that is quite a list you have there mom." I said filling up my plate.
"Don't worry if we work together we will be able to get it done in no time." Matt replied filling up his plate as well.
We all ate breakfast together and talked about the items on the list, things like clean the garage and trim hedges. Mom wanted us out of the house; she was planning on scrubbing the floors today and shampooing the carpets.
Matt and I went outside and got right to work on the garage, the thing that would take the longest. It took us nearly two hours to clean out the old junk and get the place good and cleaned up. Then Matt went to work on the hedges and I moaned the lawn, Matt finished the hedges before I finished the lawn so he went to work trimming the shrubs.
The yard work was finally done, and then a big truck pulled into the driveway, my mother had us clean the garage for a reason. She got the firewood for the fireplace on sale this time of year so she had it delivered. The guy dumped it in the driveway and Matt and I had to put it in the garage neatly stacked so it would be there for next winter.
When we finally came in we made sure we left our shoes in the foyer and came into the house. My mother was on her knees bent over wrapping the cord around her shampooer. A pink lace thong stuck out from her sweat pants making Matt and I giggle for a moment.
"You boys finally finished, let me get this stuff put away and then the three of us need to shower, I will order pizza for dinner." She said.